Methaqualone hydriodide

First approved in 1962

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H14N2O.HI
Molecular Weight	378.2076
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

I.CC1=CC=CC=C1N2C(C)=NC3=C(C=CC=C3)C2=O

InChI

InChIKey=OBQYYSKVWRKCRX-UHFFFAOYSA-N

InChI=1S/C16H14N2O.HI/c1-11-7-3-6-10-15(11)18-12(2)17-14-9-5-4-8-13(14)16(18)19;/h3-10H,1-2H3;1H

HIDE SMILES / InChI

Molecular Formula	C16H14N2O
Molecular Weight	250.2952
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	HI
Molecular Weight	127.91241
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugs.com/illicit/quaaludes.html
Curator's Comment: description was created based on several sources, including: http://www.encyclopedia.com/science/applied-and-social-sciences-magazines/methaqualone | https://www.ncbi.nlm.nih.gov/pubmed/26056160 | https://addictionlibrary.org/prescription/mandrax-uses-symptoms-signs-and-addiction-treatment.html

Methaqualone is a depressant that modulates the activity of the GABA receptors in the brain and nervous system. It promotes relaxation, sleepiness and sometimes a feeling of euphoria. It causes a drop in blood pressure and slows the pulse rate. These properties are the reason why it was initially thought to be a useful sedative and anxiolytic. Common side effects of Methaqualone include dizziness, nausea, vomiting, diarrhea, abdominal cramps, fatigue, itching, rashes, sweating, dry mouth, tingling sensation in arms and legs, seizures and its depressant effects include reduced heart rate and respiration. The drug became banned in many countries and was withdrawn from many markets in the early 1980s.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
GABA A receptor alpha-6/beta-1/delta 3 Target ID: GABA A receptor alpha-6/beta-1/delta Sources: https://www.ncbi.nlm.nih.gov/pubmed/26056160	Negative Allosteric Modulator 43	4.0 null [pEC50]
GABA A receptor alpha-4/beta-2/delta 3 Target ID: GABA A receptor alpha-4/beta-2/delta Sources: https://www.ncbi.nlm.nih.gov/pubmed/26056160	Positive Allosteric Modulator 186	4.17 null [pEC50]
GABA A receptor alpha-4/beta-3/delta 3 Target ID: GABA A receptor alpha-4/beta-3/delta Sources: https://www.ncbi.nlm.nih.gov/pubmed/26056160	Agonist 2752	3.91 null [pEC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 111 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13733024	Primary		Approved 8583	Quaalude Approved Use Methaqualone is indicated for the treatment of anxiety and sleep disorders. Launch Date 1954
Anxiety 275 Sources: https://www.drugs.com/illicit/quaaludes.html	Primary		Approved 8583	Quaalude Approved Use Methaqualone is indicated for the treatment of anxiety and sleep disorders. Launch Date 1954

C_max

Value	Dose	Co-administered	Analyte	Population
3.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4427217/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		METHAQUALONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

AUC

Value	Dose	Co-administered	Analyte	Population
46.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4427217/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		METHAQUALONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
19 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4427217/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		METHAQUALONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A1 389 CYP1A2 1197 CYP2C19 1119 CYP2A6 626 CYP2B6 776 CYP2C8 810 CYP2E1 729 CYP4A 3

Drug as victim

Target	Modality	Activity
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12900872/	likely
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12900872/	likely
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12900872/	likely
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12900872/	likely
CYP3A4 1946	substrate 4014 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000072446, https://pubmed.ncbi.nlm.nih.gov/12900872/	major
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12900872/	minor
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12900872/	no
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12900872/	no
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12900872/	no
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12900872/	no
CYP4A 3	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12900872/	no

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6821	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6821
eMolecules	757583	https://www.emolecules.com/cgi-bin/more?vid=757583
ZINC	ZINC000002568176	http://zinc15.docking.org/substances/ZINC000002568176

PubMed

Title	Date	PubMed
Retrospective cohort study of a new infant formula during the first 6 months of life: reflections on growth curves, human milk and formula feeding.	2010-11	21243867
HypoCol (red yeast rice) lowers plasma cholesterol - a randomized placebo controlled study.	2010-08	20636227
Semiautomatic quantification of angiogenesis.	2010-07	19345375
The Summary Index of Malaria Surveillance (SIMS): a stable index of malaria within India.	2010-02-11	20181218
A new recurring chromosome 13 abnormality in two older patients with de novo acute myeloid leukemia: An Indian experience.	2009-09	21088719
Rosiglitazone: can meta-analysis accurately estimate excess cardiovascular risk given the available data? Re-analysis of randomized trials using various methodologic approaches.	2009-01-10	19134216
A case of acute myeloid leukemia-M2 with trisomy 4 in addition to t(8;21).	2008-01	20300287
Chinese red yeast rice (Monascus purpureus) for primary hyperlipidemia: a meta-analysis of randomized controlled trials.	2006-11-23	17302963
Molecular epidemiology of multidrug-resistant tuberculosis, New York City, 1995-1997.	2002-11	12453347
A survey of reported synthesis of methaqualone and some positional and structural isomers.	2001-11-01	11672968
Synthesis and anticonvulsant activity of some new 2-substituted 3-aryl-4(3H)-quinazolinones.	1990-01	2296016
Seven cases of somnambulism induced by drugs.	1979-07	453369
Extrapyramidal reaction in a patient on combined drug therapy: report of a case.	1971-07-01	5284823

Patents

Sample Use Guides

In Vivo Use Guide

75-150 mg sedation. A commonly prescribed dose was 300 mg. Up to 600 mg was used for strong sedation.

Route of Administration: Oral

In Vitro Use Guide

Methaqualone displayed bell-shaped concentration-response curves as a positive allosteric modulator at all receptors when coapplied with GABA EC10 in concentrations ranging from 1 to 1000 uM (exemplified for a1b2g2S and a6b2delta. Pronounced rebound currents were observed at methaqualone concentrations of 300 uM and greater.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 10:14:42 GMT 2025` Edited by `admin` on `Wed Apr 02 10:14:42 GMT 2025`
Record UNII	7T92ANA7AZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Methaqualone hydriodide

Common Name

English

4(3H)-Quinazolinone, 2-methyl-3-(2-methylphenyl)-, hydriodide

Preferred Name

English

4(3H)-Quinazolinone, 2-methyl-3-o-tolyl-, monohydriodide

Systematic Name

English

Code System Code Type Description

CAS

19326-27-3

Created by admin on Wed Apr 02 10:14:42 GMT 2025 , Edited by admin on Wed Apr 02 10:14:42 GMT 2025

PRIMARY

FDA UNII

7T92ANA7AZ

Created by admin on Wed Apr 02 10:14:42 GMT 2025 , Edited by admin on Wed Apr 02 10:14:42 GMT 2025

PRIMARY

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Details

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Approved Use

Launch Date

Cmax

AUC

T1/2

Overview

OverviewOther

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2